SG181439A1 - Imidazopyridine derivatives as jak inhibitors - Google Patents
Imidazopyridine derivatives as jak inhibitors Download PDFInfo
- Publication number
- SG181439A1 SG181439A1 SG2012038238A SG2012038238A SG181439A1 SG 181439 A1 SG181439 A1 SG 181439A1 SG 2012038238 A SG2012038238 A SG 2012038238A SG 2012038238 A SG2012038238 A SG 2012038238A SG 181439 A1 SG181439 A1 SG 181439A1
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- SG
- Singapore
- Prior art keywords
- group
- pyridin
- alkyl
- branched
- linear
- Prior art date
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- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title abstract 2
- 229940122245 Janus kinase inhibitor Drugs 0.000 title description 16
- 108010024121 Janus Kinases Proteins 0.000 claims abstract description 43
- 102000015617 Janus Kinases Human genes 0.000 claims abstract description 43
- 239000003112 inhibitor Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 626
- 125000000623 heterocyclic group Chemical group 0.000 claims description 374
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 343
- 125000001072 heteroaryl group Chemical group 0.000 claims description 324
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 323
- 125000005843 halogen group Chemical group 0.000 claims description 306
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 302
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 263
- 125000001188 haloalkyl group Chemical group 0.000 claims description 252
- 229910052799 carbon Inorganic materials 0.000 claims description 243
- 125000001424 substituent group Chemical group 0.000 claims description 235
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 claims description 229
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 205
- 125000005842 heteroatom Chemical group 0.000 claims description 204
- 229910052757 nitrogen Inorganic materials 0.000 claims description 164
- -1 hydroxyalkyl-phenyl Chemical group 0.000 claims description 160
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 159
- 229910052760 oxygen Inorganic materials 0.000 claims description 159
- 229910052717 sulfur Inorganic materials 0.000 claims description 156
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 147
- 125000003118 aryl group Chemical group 0.000 claims description 138
- 125000002950 monocyclic group Chemical group 0.000 claims description 133
- 125000003545 alkoxy group Chemical group 0.000 claims description 112
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 71
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 125000004076 pyridyl group Chemical group 0.000 claims description 58
- 125000000468 ketone group Chemical group 0.000 claims description 54
- 229910052792 caesium Inorganic materials 0.000 claims description 51
- LRJOKNYELSECDZ-UHFFFAOYSA-N imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=C(C#N)C=CC2=NC=CN21 LRJOKNYELSECDZ-UHFFFAOYSA-N 0.000 claims description 50
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 47
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 46
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 45
- 229920006395 saturated elastomer Polymers 0.000 claims description 44
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 201000010099 disease Diseases 0.000 claims description 34
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 31
- 125000003386 piperidinyl group Chemical group 0.000 claims description 26
- 125000003367 polycyclic group Chemical group 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 26
- 206010028980 Neoplasm Diseases 0.000 claims description 25
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 20
- 230000005764 inhibitory process Effects 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 18
- YSPVHAUJXLGZHP-UHFFFAOYSA-N ethyl piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCCC1 YSPVHAUJXLGZHP-UHFFFAOYSA-N 0.000 claims description 18
- 230000001575 pathological effect Effects 0.000 claims description 18
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 208000014767 Myeloproliferative disease Diseases 0.000 claims description 15
- 206010052779 Transplant rejections Diseases 0.000 claims description 15
- KIYOXVPZRXLLDR-UHFFFAOYSA-N imidazo[1,2-a]pyridine-7-carbonitrile Chemical compound C1=C(C#N)C=CN2C=CN=C21 KIYOXVPZRXLLDR-UHFFFAOYSA-N 0.000 claims description 15
- 230000001404 mediated effect Effects 0.000 claims description 15
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 208000032839 leukemia Diseases 0.000 claims description 14
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 14
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 14
- SSNHGLKFJISNTR-DYSNNVSPSA-N (6ar,10ar)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol;2-[(1r,6r)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1.C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 SSNHGLKFJISNTR-DYSNNVSPSA-N 0.000 claims description 13
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 13
- 210000001185 bone marrow Anatomy 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 102000005962 receptors Human genes 0.000 claims description 13
- 108020003175 receptors Proteins 0.000 claims description 13
- 125000000335 thiazolyl group Chemical group 0.000 claims description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- 201000004681 Psoriasis Diseases 0.000 claims description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 210000000056 organ Anatomy 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 208000027866 inflammatory disease Diseases 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 10
- 150000001204 N-oxides Chemical class 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 10
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 10
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 10
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
- 206010046851 Uveitis Diseases 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 9
- 230000036210 malignancy Effects 0.000 claims description 9
- 201000006417 multiple sclerosis Diseases 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- MWQIPXGWZWKNRF-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptan-5-amine Chemical compound C1NC2C(N)CC1C2 MWQIPXGWZWKNRF-UHFFFAOYSA-N 0.000 claims description 8
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 8
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 7
- 206010013774 Dry eye Diseases 0.000 claims description 7
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- 125000001425 triazolyl group Chemical group 0.000 claims description 7
- NZOASCIAGZGVKC-UHFFFAOYSA-N 3-[4-[(5-hydroxy-2-adamantyl)amino]pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(C=3N=CC=C(N=3)NC3C4CC5CC(C4)(CC3C5)O)=CN=C21 NZOASCIAGZGVKC-UHFFFAOYSA-N 0.000 claims description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 201000008937 atopic dermatitis Diseases 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 150000004675 formic acid derivatives Chemical class 0.000 claims description 6
- IEOADZOTWIMSMC-UHFFFAOYSA-N imidazo[1,2-a]pyridin-6-ylmethanol Chemical compound C1=C(CO)C=CC2=NC=CN21 IEOADZOTWIMSMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- HNJBEVLQSNELDL-YZRHJBSPSA-N pyrrolidin-2-one Chemical group O=C1CC[14CH2]N1 HNJBEVLQSNELDL-YZRHJBSPSA-N 0.000 claims description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 5
- JQDFGZKKXBEANU-IMJSIDKUSA-N Ala-Cys Chemical compound C[C@H](N)C(=O)N[C@@H](CS)C(O)=O JQDFGZKKXBEANU-IMJSIDKUSA-N 0.000 claims description 5
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 5
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 5
- 201000010105 allergic rhinitis Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- OMOYEBFTSROFJD-UHFFFAOYSA-N 3-[4-[(4-fluorophenyl)methylamino]pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(F)=CC=C1CNC1=CC=NC(C=2N3C=C(C=CC3=NC=2)C#N)=N1 OMOYEBFTSROFJD-UHFFFAOYSA-N 0.000 claims description 4
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- XBZUZUSLFNFXKP-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-2-imidazo[1,2-a]pyridin-3-yl-6-pyridin-3-ylpyrimidin-4-amine Chemical compound N=1C(C=2N3C=CC=CC3=NC=2)=NC(NCC(C)(C)C)=CC=1C1=CC=CN=C1 XBZUZUSLFNFXKP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- HVVNJUAVDAZWCB-UHFFFAOYSA-N prolinol Chemical compound OCC1CCCN1 HVVNJUAVDAZWCB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- REUAXQZIRFXQML-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1CC2C(N)CN1CC2 REUAXQZIRFXQML-UHFFFAOYSA-N 0.000 claims description 3
- SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical group CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 claims description 3
- DFVSSUKNZSTAOM-ZDUSSCGKSA-N 2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)-n-[(1s)-1-phenylethyl]pyrimidin-4-amine Chemical compound C1([C@@H](NC=2N=C(N=CC=2)C=2N3C=C(F)C=CC3=NC=2)C)=CC=CC=C1 DFVSSUKNZSTAOM-ZDUSSCGKSA-N 0.000 claims description 3
- UQXWQOLPSDIYST-UHFFFAOYSA-N 2-[4-(2,2-dimethylpropylamino)quinazolin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=C(C#N)C=CC2=NC(C=3N=C(C4=CC=CC=C4N=3)NCC(C)(C)C)=CN21 UQXWQOLPSDIYST-UHFFFAOYSA-N 0.000 claims description 3
- YSZBDKVUCCYTAE-CQSZACIVSA-N 3,3,3-trifluoro-1-[(3r)-3-[[2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidin-4-yl]-methylamino]piperidin-1-yl]propan-1-one Chemical compound C=1C=NC(C=2N3C=C(F)C=CC3=NC=2)=NC=1N(C)[C@@H]1CCCN(C(=O)CC(F)(F)F)C1 YSZBDKVUCCYTAE-CQSZACIVSA-N 0.000 claims description 3
- LGHSLSUKFHSZPO-GFCCVEGCSA-N 3,3,3-trifluoro-1-[(3r)-3-[[5-fluoro-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidin-4-yl]amino]piperidin-1-yl]propan-1-one Chemical compound N12C=C(F)C=CC2=NC=C1C(N=1)=NC=C(F)C=1N[C@@H]1CCCN(C(=O)CC(F)(F)F)C1 LGHSLSUKFHSZPO-GFCCVEGCSA-N 0.000 claims description 3
- ULKILXZOJXXOJO-UHFFFAOYSA-N 3-[4-(2,2-dimethylpropylamino)pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound CC(C)(C)CNC1=CC=NC(C=2N3C=C(C=CC3=NC=2)C#N)=N1 ULKILXZOJXXOJO-UHFFFAOYSA-N 0.000 claims description 3
- JVPAURGXWZAKBL-UHFFFAOYSA-N 3-[4-(2-methoxyethylamino)pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound COCCNC1=CC=NC(C=2N3C=C(C=CC3=NC=2)C#N)=N1 JVPAURGXWZAKBL-UHFFFAOYSA-N 0.000 claims description 3
- BYBLMIKOGPGCIO-UHFFFAOYSA-N 3-[4-(cyclohexylmethylamino)pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound N12C=C(C#N)C=CC2=NC=C1C(N=1)=NC=CC=1NCC1CCCCC1 BYBLMIKOGPGCIO-UHFFFAOYSA-N 0.000 claims description 3
- JIMWEDIPGVNLPG-UHFFFAOYSA-N 3-[4-[(3-fluorophenyl)methylamino]pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound FC1=CC=CC(CNC=2N=C(N=CC=2)C=2N3C=C(C=CC3=NC=2)C#N)=C1 JIMWEDIPGVNLPG-UHFFFAOYSA-N 0.000 claims description 3
- SUQUOHWKSUQBAN-UHFFFAOYSA-N 3-[4-[(8-fluoro-3,4-dihydro-2h-chromen-4-yl)amino]pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(C=3N=CC=C(N=3)NC3C=4C=CC=C(C=4OCC3)F)=CN=C21 SUQUOHWKSUQBAN-UHFFFAOYSA-N 0.000 claims description 3
- CCIBUKBOBXOPGP-UHFFFAOYSA-N 3-[4-[4-(2-cyanoacetyl)-1,4-diazepan-1-yl]pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1CN(C(CC#N)=O)CCCN1C1=CC=NC(C=2N3C=C(C=CC3=NC=2)C#N)=N1 CCIBUKBOBXOPGP-UHFFFAOYSA-N 0.000 claims description 3
- ZPFFLSDYSZDFFD-GOSISDBHSA-N 3-[4-[[(3r)-1-(5-cyanopyridine-2-carbonyl)piperidin-3-yl]amino]pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C([C@@H](CCC1)NC=2N=C(N=CC=2)C=2N3C=C(C=CC3=NC=2)C#N)N1C(=O)C1=CC=C(C#N)C=N1 ZPFFLSDYSZDFFD-GOSISDBHSA-N 0.000 claims description 3
- GQIZKYDGWZJEGF-UHFFFAOYSA-N 3-[4-[benzyl(methyl)amino]pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C=1C=NC(C=2N3C=C(C=CC3=NC=2)C#N)=NC=1N(C)CC1=CC=CC=C1 GQIZKYDGWZJEGF-UHFFFAOYSA-N 0.000 claims description 3
- KPGFSQWASKHKES-UHFFFAOYSA-N 3-[5-bromo-4-(2,2-dimethylpropylamino)pyrimidin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=C(Br)C(NCC(C)(C)C)=NC(C=2N3C=C(C=CC3=NC=2)C#N)=N1 KPGFSQWASKHKES-UHFFFAOYSA-N 0.000 claims description 3
- CXGIOHOUKRXVOX-UHFFFAOYSA-N 3-[6-(cyclohexylmethylamino)pyrazin-2-yl]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound N12C=C(C#N)C=CC2=NC=C1C(N=1)=CN=CC=1NCC1CCCCC1 CXGIOHOUKRXVOX-UHFFFAOYSA-N 0.000 claims description 3
- OSFMNRTYASWFNU-ZDUSSCGKSA-N 6-(6-fluoroimidazo[1,2-a]pyridin-3-yl)-n-[(1s)-1-phenylethyl]pyrazin-2-amine Chemical compound C1([C@@H](NC=2N=C(C=NC=2)C=2N3C=C(F)C=CC3=NC=2)C)=CC=CC=C1 OSFMNRTYASWFNU-ZDUSSCGKSA-N 0.000 claims description 3
- DJVCCPIKXAYQGA-AWEZNQCLSA-N 6-imidazo[1,2-a]pyridin-3-yl-n-[(1s)-1-phenylethyl]pyrazin-2-amine Chemical compound C1([C@@H](NC=2N=C(C=NC=2)C=2N3C=CC=CC3=NC=2)C)=CC=CC=C1 DJVCCPIKXAYQGA-AWEZNQCLSA-N 0.000 claims description 3
- CFULKORJNOQVFQ-HDJSIYSDSA-N C1C[C@@H](O)CC[C@@H]1NC1=CC=NC(C=2N3C=C(C=CC3=NC=2)C#N)=N1 Chemical compound C1C[C@@H](O)CC[C@@H]1NC1=CC=NC(C=2N3C=C(C=CC3=NC=2)C#N)=N1 CFULKORJNOQVFQ-HDJSIYSDSA-N 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 108010050904 Interferons Proteins 0.000 claims description 3
- 102000014150 Interferons Human genes 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 3
- ONOJJCTXSDBVSP-UHFFFAOYSA-N imidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound C1=C(C(=O)O)C=CC2=NC=CN21 ONOJJCTXSDBVSP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 229940047124 interferons Drugs 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- UWOBONKIYHUMEC-KRWDZBQOSA-N n-[(1s)-1-phenylethyl]-6-(6-pyridin-3-ylimidazo[1,2-a]pyridin-3-yl)pyrazin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=CN=CC=1C(N1C=2)=CN=C1C=CC=2C1=CC=CN=C1 UWOBONKIYHUMEC-KRWDZBQOSA-N 0.000 claims description 3
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Classifications
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
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Applications Claiming Priority (3)
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EP09382303A EP2338888A1 (en) | 2009-12-24 | 2009-12-24 | Imidazopyridine derivatives as JAK inhibitors |
US29029309P | 2009-12-28 | 2009-12-28 | |
PCT/EP2010/007913 WO2011076419A1 (en) | 2009-12-24 | 2010-12-23 | Imidazopyridine derivatives as jak inhibitors |
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SG10201407927UA SG10201407927UA (en) | 2009-12-24 | 2010-12-23 | Imidazopyridine derivatives as jak inhibitors |
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SG10201407927UA SG10201407927UA (en) | 2009-12-24 | 2010-12-23 | Imidazopyridine derivatives as jak inhibitors |
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US (1) | US20130216498A1 (ko) |
EP (2) | EP2338888A1 (ko) |
JP (1) | JP2013515688A (ko) |
KR (1) | KR20120118459A (ko) |
CN (1) | CN102695706A (ko) |
AR (1) | AR079689A1 (ko) |
AU (1) | AU2010335556A1 (ko) |
BR (1) | BR112012015540A2 (ko) |
CA (1) | CA2785113A1 (ko) |
CL (1) | CL2012001379A1 (ko) |
CO (1) | CO6541643A2 (ko) |
CR (1) | CR20120334A (ko) |
EA (1) | EA201200938A1 (ko) |
EC (1) | ECSP12011910A (ko) |
GT (1) | GT201200207A (ko) |
IL (1) | IL219916A0 (ko) |
MX (1) | MX2012007175A (ko) |
NZ (1) | NZ599932A (ko) |
PE (1) | PE20121482A1 (ko) |
SG (2) | SG181439A1 (ko) |
TW (1) | TWI481608B (ko) |
UA (1) | UA107951C2 (ko) |
UY (1) | UY33130A (ko) |
WO (1) | WO2011076419A1 (ko) |
ZA (1) | ZA201203326B (ko) |
Families Citing this family (35)
Publication number | Priority date | Publication date | Assignee | Title |
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UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
AU2011246067A1 (en) * | 2010-04-28 | 2012-09-27 | Daiichi Sankyo Company, Limited | [5,6] heterocyclic compound |
EP2463289A1 (en) | 2010-11-26 | 2012-06-13 | Almirall, S.A. | Imidazo[1,2-b]pyridazine derivatives as JAK inhibitors |
US9029389B2 (en) | 2011-04-21 | 2015-05-12 | Institut Pasteur Korea | Anti-inflammation compounds |
EP2554544A1 (en) | 2011-08-01 | 2013-02-06 | Almirall, S.A. | Pyridin-2(1h)-one derivatives as jak inhibitors |
WO2014114928A1 (en) | 2013-01-23 | 2014-07-31 | Astrazeneca Ab | Chemical compounds |
PT3269716T (pt) * | 2013-03-14 | 2020-10-09 | Galapagos Nv | Novos compostos e suas composições farmacêuticas para o tratamento de doenças inflamatórias |
WO2015089218A1 (en) * | 2013-12-10 | 2015-06-18 | David Wustrow | Monocyclic pyrimidine/pyridine compounds as inhibitors of p97 complex |
WO2015091531A1 (en) * | 2013-12-19 | 2015-06-25 | Almirall, S.A. | Imidazolopyrimidin-2-yl derivatives as jak inhibitors |
CN106458996B (zh) | 2014-01-20 | 2020-11-03 | 克里弗生物科学公司 | 作为p97复合物的抑制剂的稠合嘧啶 |
US9775839B2 (en) | 2014-03-13 | 2017-10-03 | Merck Sharp & Dohme Corp. | 2-pyrazine carboxamides as spleen tyrosine kinase inhibitors |
TWI679205B (zh) | 2014-09-02 | 2019-12-11 | 日商日本新藥股份有限公司 | 吡唑并噻唑化合物及醫藥 |
FR3030521B1 (fr) * | 2014-12-23 | 2019-07-26 | Galderma Research & Development | Nouveaux composes heterocycliques et leur utilisation en medecine ainsi qu'en cosmetique |
EP3250572B1 (en) * | 2015-01-28 | 2020-08-26 | Shanghai Fudan-Zhangjiang Bio-Pharmaceutical Co., Ltd. | Substituted imidazo [1, 2-a]pyridin-2-ylamine compounds, and pharmaceutical compositions and methods of use thereof |
TW201705961A (zh) | 2015-06-11 | 2017-02-16 | 阿爾米雷爾有限公司 | 作為jak抑制劑的2-(吡唑并吡啶-3-基)嘧啶衍生物 |
UA123633C2 (uk) | 2015-11-03 | 2021-05-05 | Тереванс Байофарма Ар Енд Ді Айпі, Елелсі | Сполуки інгібітору jak-кінази для лікування респіраторного захворювання |
TWI712604B (zh) | 2016-03-01 | 2020-12-11 | 日商日本新藥股份有限公司 | 具jak抑制作用之化合物之結晶 |
EP3468953B1 (en) | 2016-06-13 | 2024-05-22 | GlaxoSmithKline Intellectual Property Development Limited | Substituted pyridines as inhibitors of dnmt1 |
WO2018013430A2 (en) | 2016-07-12 | 2018-01-18 | Arisan Therapeutics Inc. | Heterocyclic compounds for the treatment of arenavirus infection |
SG11201907840RA (en) | 2017-03-09 | 2019-09-27 | Theravance Biopharma R&D Ip Llc | Fused imidazo-piperidine jak inhibitors |
TW201900170A (zh) | 2017-05-01 | 2019-01-01 | 美商施萬生物製藥研發 Ip有限責任公司 | 使用jak抑制劑化合物之治療方法 |
CA3089769A1 (en) * | 2018-01-29 | 2019-08-01 | Merck Patent Gmbh | Gcn2 inhibitors and uses thereof |
WO2020092015A1 (en) | 2018-11-02 | 2020-05-07 | University Of Rochester | Therapeutic mitigation of epithelial infection |
CN112739689B (zh) * | 2018-12-07 | 2022-06-03 | 优迈特株式会社 | 含氟嘧啶化合物及其制造方法 |
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2009
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2010
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- 2010-12-21 UY UY0001033130A patent/UY33130A/es unknown
- 2010-12-22 AR ARP100104869A patent/AR079689A1/es unknown
- 2010-12-23 EP EP10803058A patent/EP2516436A1/en not_active Withdrawn
- 2010-12-23 EA EA201200938A patent/EA201200938A1/ru unknown
- 2010-12-23 KR KR1020127016404A patent/KR20120118459A/ko not_active Application Discontinuation
- 2010-12-23 SG SG2012038238A patent/SG181439A1/en unknown
- 2010-12-23 MX MX2012007175A patent/MX2012007175A/es not_active Application Discontinuation
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- 2010-12-23 WO PCT/EP2010/007913 patent/WO2011076419A1/en active Application Filing
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- 2010-12-23 AU AU2010335556A patent/AU2010335556A1/en not_active Abandoned
- 2010-12-23 BR BR112012015540A patent/BR112012015540A2/pt not_active IP Right Cessation
- 2010-12-23 CA CA2785113A patent/CA2785113A1/en not_active Abandoned
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- 2010-12-23 PE PE2012000863A patent/PE20121482A1/es not_active Application Discontinuation
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CA2785113A1 (en) | 2011-06-30 |
UA107951C2 (en) | 2015-03-10 |
ZA201203326B (en) | 2013-03-27 |
UY33130A (es) | 2011-06-30 |
TW201130835A (en) | 2011-09-16 |
JP2013515688A (ja) | 2013-05-09 |
AR079689A1 (es) | 2012-02-15 |
IL219916A0 (en) | 2012-07-31 |
TWI481608B (zh) | 2015-04-21 |
AU2010335556A1 (en) | 2012-05-31 |
US20130216498A1 (en) | 2013-08-22 |
MX2012007175A (es) | 2012-07-04 |
EA201200938A1 (ru) | 2013-02-28 |
CN102695706A (zh) | 2012-09-26 |
ECSP12011910A (es) | 2012-07-31 |
KR20120118459A (ko) | 2012-10-26 |
GT201200207A (es) | 2015-02-19 |
WO2011076419A1 (en) | 2011-06-30 |
BR112012015540A2 (pt) | 2019-09-24 |
SG10201407927UA (en) | 2015-01-29 |
PE20121482A1 (es) | 2012-11-05 |
EP2338888A1 (en) | 2011-06-29 |
CO6541643A2 (es) | 2012-10-16 |
CR20120334A (es) | 2012-10-05 |
NZ599932A (en) | 2014-08-29 |
CL2012001379A1 (es) | 2012-10-12 |
EP2516436A1 (en) | 2012-10-31 |
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